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TAKAKI, M. Metabolomic study of fungi of the genus Colletotrichum and tambjamines-producing marine organisms. 2020. 248 p. Thesis (PhD) – Instituto de Química de São Carlos, Universidade de São Paulo, São Carlos, 2020. The present study describes the metabolomic investigation of fungi of the genus Colletotrichum and tambjamine-producing marine organisms Virididentula dentata, Tambja stegosauriformis, Tambja brasiliensis and Roboastra ernsti. Fungi belonging to the genus Colletotrichum cause disease in a wide variety of plants from different families. Secondary metabolites produced by these microorganisms can be part of the virulence process associated with their phytopathogenicity. Although many metabolites of Colletotrichum spp. have already been isolated and identified, the phytopathogenicity associated with fungi of this genus is not yet well established. In order to investigate the metabolic differences between endophytic and phytopathogenic strains of Colletotrichum spp., culture media produced by twentyfive isolates of Colletotrichum spp. were investigated, 16 of which were endophytic and 9 were phytopathogenic. The culture media were fractionated and analyzed by UPLC-IMS-QToF-HRMS. The raw data were processed using in-house tools and molecular networking. The evaluation of the results allowed us to conclude that endophytic and phytopathogenic strains of Colletotrichum spp. have considerably different metabolism. Endophytic strains produce compounds that are common to several strains in the group; phytopathogenic strains produce compounds more specific to each isolate. Dereplication of the GNPS exported results using an inhouse library of compounds isolated from Colletotrichum fungi combined with in-silico fragmentation tools allowed the identification of 5 compounds in samples related to phytopathogenic strains. Those compounds display phytotoxic activity. Such results are a strong indication that the phytopathogenicity of Colletotrichum fungi may be associated with the production of phytotoxic compounds. Tambjamines are a group of alkaloids chemically related to prodigiosin and prodiginine, isolated from bacteria and marine organisms such as ascidians, bryozoans and nudibranchs. In addition to presenting diversified biological activities, tambjaminas are possibly related to the defense mechanisms of the organisms from which they are isolated. Several studies of tambjamine-producing marine organisms involved in prey-predator relationships have shown that these alkaloids were detected in extracts from both prey and predators. In this sense, extracts of V. dentata, T. stegosauriformis, T. brasiliensis and R. ernsti were obtained. The analysis of organic and aqueous extracts from marine organisms by HPLC-UV-ELSD-MS and UPLC-QToF-MS/MS allowed us to confirm the presence of 6 known tambjamines: tambjamines A, C, D and K, and the aldehydes of the tambjamines A and B. The quantification of tambjamine content in samples from different invertebrates performed by HPLC with a fluorescence detector demonstrated that T. stegosauriformis and T. brasiliensis have tambjamines content 8 and 14 times higher than their prey V. dentata, while R. ernsti has tambjamines concentration between 3 and 5 times higher than their prey T. brasiliensis and T. stegosauriformis. Additionally, non-targeted metabolomic analyses of the extract from the mantle of R. ernsti allowed to verify the presence of 6 new tambjamines. The synthesis, purification and characterization of the new tambjamines allowed to confirm the structure of one of the unprecedented tambjamines.

Estudo metabolômico de fungos do gênero >i<Colletotrichum>/i< e de organismos marinhos produtores de tambjaminas